Search Middletown Cottages

Check prices for these dates

In two weeks
Feb 20 - Feb 22
In two months
Apr 3 - Apr 5
In three months
May 1 - May 3
In four months
May 29 - May 31

Our top choices for Middletown cottages

Exterior

Hello Small Stone

Hello Small Stone
Middletown
9.6 out of 10, Exceptional, (5 reviews)
"The house was great. It was nice to sit and relax by the small pond in the back."
United States
John H.
$384 nightly
The price is $434
Mar 4 - Mar 5
Total with taxes and fees
Hello Small Stone
Exterior

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Kerhonkson
9.4 out of 10, Exceptional, (12 reviews)
"Charming and relaxing cottage. Perfect location for hiking or enjoying Lake Minnewaska or Mohonk Preserve. "
United States
Patrick S.
$191 nightly
The price is $194
Feb 11 - Feb 12
Total with taxes and fees
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Smart TV

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful location. We really enjoyed seeing the deer in the field every morning. "
United States
Aaron M.
$281 nightly
The price is $293
Feb 8 - Feb 9
Total with taxes and fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Exterior

Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around

Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around
Sparrow Bush
9.4 out of 10, Exceptional, (11 reviews)
"A little off the beaten path, but a lovely Vrbo with excellent amenities with a nice natural surrounding."
United States
Nicholas G.
$260 nightly
The price is $294
Feb 24 - Feb 25
Total with taxes and fees
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (131 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
$269 nightly
The price is $304
Feb 8 - Feb 9
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Outdoor dining

Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike

Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Vernon Township
8.8 out of 10, Excellent, (3 reviews)
"House was beautiful! Airy, cool and bedrooms were comfortable! Such a cute cottage and outdoor fire pit was amazing."
United States
Cherlyn I.
$423 nightly
The price is $478
Feb 9 - Feb 10
Total with taxes and fees
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Middletown Hotel Reviews

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

10/10 Excellent
"Nice hotel. Great staff. "
Ian 7-night trip
Posted 10 hours ago
Sleep Inn & Suites Monroe - Woodbury

Find out more about Middletown

Middletown Cottages information

Number of reviews
156
Accommodation
134 Cottages
Lowest Price
$194
Highest Price
$478

Frequently asked questions

Why book your cottage in Middletown with Expedia?
We think a getaway should be a walk in the park, so if you're seeking cottages in Middletown at a competitive rate, Expedia has got your back. Keep costs down and select an inexpensive option far from the downtown buzz, or splurge on a 5-star cottage to spoil your loved ones.
How can I find cheap cottages in Middletown?
With Expedia's useful filter tool, sourcing cheap cottages in Middletown is a cinch. To discover accommodations that'll make your wallet smile, narrow down your search by budget, amenities and star rating.
What is there to do in Middletown near my cottage?
If you'd like to see the sights of Middletown, be sure to visit Orange County Fair Speedway. It's a hit among visitors and locals alike.

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